1) Luis Enrique, Real Madrid to Barcelona (1996)

In a competition to find the most famous Luis to play for both Barcelona and Real Madrid, there is only ever going to be one winner. The sight of a pig's head lying by the Camp Nou pitch after being flung towards Luis Figo by Barcelona fans seething about his move to the Spanish capital in 2000 remains one of the most iconic and extraordinary moments in Clásico history, one that vividly sums up the hatred that exists between the two clubs. No one will ever forget it and even now, a decade on, it is an incident that provokes bafflement, a shake of the head and, if we are being totally honest, a guilty chuckle.

Of course, Figo was not the first player to cross the divide. He was not even the first Luis. The only difference, though, was that Luis Enrique moved in the other direction, joining Barcelona from Real Madrid on a free transfer in 1996, and unlike Figo he revelled in the abuse that inevitably came his way. He enjoyed nothing more than winding up Madrid fans and had no problem with the cries of "Hijo de puta" that flew from the stands when he returned to the Bernabéu.

Luis Enrique, perhaps the greatest defender/midfielder/forward (R/L/C) of all time, had no affiliation to Barcelona initially. He was born in Asturias and began his career with his local club, Sporting Gijon, before signing for Madrid in 1991. He spent five years there and even scored the fourth in a 5-0 Clásico win in the 1994-95 season, a year in which Madrid claimed their first La Liga title for five years. He celebrated wildly.

Yet in 1996 he left and joined Barcelona, who he represented for eight largely successful years before his retirement in 2004. His departure rankled in Madrid. When the two clubs met in 1997, Marca made sure to point out that he was "a traitor … and we all know what happens to them". Indeed we do – they turn up at the Bernabéu and they score. Perhaps what hurt most was that Luis Enrique could play too. "I felt he was unbelievable as a player, also a rare guy with a great spirit," said Sir Bobby Robson, one of his managers at Barcelona. "He could fill holes all the time and perform exquisitely."

Goals against Madrid were a regular occurrence and Luis Enrique liked nothing more than "kissing the Catalan shield on his shirt whenever he scores against his former club (he is not a Catalan – no matter) or telling the press how happy he is to live in such a vibrant and open city such as Barcelona – the implication, of course, being that Madrid is exactly the opposite," wrote Phil Ball in Morbo: The Story of Spanish Football. Luis Enrique did everything he could to stir the pot, once saying that he felt "prouder to be a culé in the Bernabéu than anywhere else".

"Luis Enrique loves to hate Madrid – and the feeling is mutual," wrote Sid Lowe in 2003. "The last time he visited, Madrid's Ultras Sur offered their own computerised version of Mole Whacking – Luis Enrique whacking, with five points and a splattering of blood for every time you hit him." By then, he had already ensured the bad blood would stain his relationship with Madrid for ever by not even bothering to RSVP after being invited to an event in February 2002 and begin the celebrations for Madrid's centenary. Of course, he made sure it was known he had plans to spend the evening washing his hair instead. Sir Alex Ferguson once said that Dennis Wise could start a fight in an empty room. Luis Enrique preferred it with 95,000 people. JS

2) Denis Law, Manchester United to Manchester City (1973)

It's March 1960, and Huddersfield Town's "20-year-old Scottish boy wonder inside-forward" Denis Law was a wee loon in demand. Newcastle United, Wolverhampton Wanderers, Manchester City, West Bromwich Albion, Birmingham City and Rangers were all feverishly preparing bids, but it looked like Arsenal would prevail, having tabled a record £50,000 offer. Their boss George Swindin had practically camped out in Huddersfield to woo Law, while extra overtures were being made by Highbury's tough-tackling right half Tommy Docherty, who had taken the young player under his wing while the two were on Scotland duty. "Denis is a great player, he is a performer in the Arsenal tradition, and it would be wonderful if he came here to play," Docherty told the press, adding that he expected Law to ring him up asking for advice, whereupon he would tell him: "If you get the chance, come to Arsenal! It's a great club!"

Law joined Manchester City instead for £55,000, and not long after the start of the following season, an outraged Docherty took to the Sunday papers to suggest that the youngster had backed the wrong horse. "Denis may regret it," he said. "He wants to stay in First Division football and if he stays with Manchester City I doubt whether he'll do that." "LAW FALLS OUT WITH HIS SOCCER PAL," screamed the Mirror a couple of days later. "I was upset when I read it," responded Law. "It's silly to talk about relegation when we have had such a good start to the season." City reported Docherty to the Football League in a fit of affronted pique.

But the generally laid-back Law, who of course eventually ended up in gainful employment across Manchester at United, was not the sort to hold grudges. He later played under Docherty on international duty, and when United boss Frank O'Farrell began to struggle in late 1972, the player was quietly approached by Sir Matt Busby for a check-up on the Doc. Law, who had been impressed with Docherty's tactical and man-management skills, gave his soccer pal the full sell. "Pretty much on my word, Manchester United went and got him," Law later recalled.

Law also later recalled this: "Four months after I helped ease him through the front door, the Doc was easing me out the back door." At the end of the 1972-73 season, Docherty summoned Law to his office and told the player that United had decided to reward him for his services with a free transfer. An initially distraught Law – 33, shocked, with a year still remaining on his contract – stated that he would rather retire with dignity while still playing for the club he loved. Docherty relented, and an agreement was struck which would see Law ostensibly play on until his testimonial at the start of the following season against European champions Ajax – which would be billed as Law v Cruyff – after which he would announce his immediate retirement. Everyone would be content enough with that.

Law, now philosophically at ease with the situation, drove north to visit family in Aberdeen, which was where, sitting in a pub the next afternoon, he heard BBC Grandstand's Football Focus announce that United had released him. He was available on a free. His hackles again raised, Law sped back down south, but by then everyone had gone off for their summer holidays. He cleared his locker with nobody to say goodbye to, only the janitor in attendance. Law would still get his money-spinning testimonial, though the 46,000 paying punters who turned up in October had reason to feel slightly short-changed: the man himself was injured and couldn't play, while Cruyff had long since buggered off for Barcelona.

Another small problem: by that point in proceedings, Law had become a City player again. Their manager Johnny Hart had approached him at a football writers' dinner, where the pair had shaken hands on a free transfer there and then. "Nobody realised a big story was right under their noses," noted Law, little surprise given the assembled hacks were ploughing through a free bar. Law, having been blessed on his way to Maine Road by Busby, went on to have a "lovely year", which ended with a valedictory appearance at the World Cup finals, though of course his most memorable act came eight minutes from the end of the domestic season, when he swung a half-hearted heel at a loose ball to score the goal that symbolically, if not literally, relegated United. Docherty's United.

Law, dignity personified, trudged off the Old Trafford pitch in despair. He never once moaned in public about how his career at United had been crudely cut short, the truth only emerging a few years later when Docherty, suing former United winger Willie Morgan for libel, told a court that Law hadn't given two hoots about the manner of his Old Trafford exit, before later admitting on oath how that hadn't exactly been the case. A reluctant Law was forced to finally give his version of events during Docherty's subsequent trial for perjury at the Old Bailey, wondering how it had all come to this, not least because, as he wryly pointed out, "Crippen's been in this dock!" SM

3) Sol Campbell, Tottenham to Arsenal (2001)

As Michael Owen streaked past Arsenal's defence to score the winning goal in the 2001 FA Cup final, Arsène Wenger knew. The famous Arsenal back four, their bodies slowing down after the strain caused by years of raising their arms in anticipation of an offside flag, was in need of renovation and – let's put this mildly – Igors Stepanovs was not the man to step in for Tony Adams. Wenger would have to work the sort of magic in the transfer market that had seen him sign Nicolas Anelka, Thierry Henry, Patrick Vieira, Marc Overmars and Emmanuel Petit in previous years.

Luckily he did not have to look too far. Just down the Seven Sisters Road, Tottenham, who had been drifting aimlessly in mid-table for years, were desperately trying to convince their captain and best player, Sol Campbell, to extend his contract, which was set to expire in the summer. It was a hard sell. Unlike now, qualifying for the Champions League was a pipe dream for Tottenham and Campbell, an England regular and one of the finest defenders in the world, was wanted by almost every major club in Europe. At the age of 26, the time had come to leave a club where he had spent his entire career.

A bitter war of words ensued. Tottenham called Campbell's wage demands "obscene". The defender hit back, saying he deserved more respect for the loyalty he had shown in the past. Barcelona, Internazionale, Liverpool all hankered after his signature. And so did Arsenal.

This was a crucial period for Wenger too. His side had not won anything since the Double in 1998 and gradually seemed to be drifting away from Manchester United, who added Ruud van Nistelrooy and Juan Sebastián Verón to a squad that had just won its third successive league title. Real Madrid wanted to sign Vieira and after the midfielder reacted coolly to the signings of Giovanni van Bronckhorst and Francis Jeffers, a statement of intent was imperative.

When it arrived at the start of July, it was deafening. A midday press conference which journalists presumed had been called to announce Richard Wright's arrival from Ipswich turned out to be far more seismic. There was Campbell, dressed in a black suit and a white shirt, strolling along with Wenger after being convinced to cross north London after a late-night visit from Arsenal's chief executive, David Dein. In doing so, Campbell became the first high-profile player to join Arsenal from Tottenham since Pat Jennings in 1977.

He defended himself by saying he needed to win trophies and that moving abroad would make it more difficult for England's new manager, Sven-Goran Eriksson, to watch him. His words fell on deaf ears. It was a move that went down as well as chicken carpaccio and when England played Holland in a friendly at White Hart Lane in August 2001, Eriksson left Campbell out. The two league titles and the three FA Cups he won during his time at Arsenal probably made up for it. JS

4) Andrea Pirlo, Milan to Juventus (2011)

They're well good, words, you can use them to make some well incongruous phrases, like "compassionate Tory turd-blancmange", or "red trousers save lives". But of the billions of combinations in the English language, there are few quite as incongruous as "teenage winger Andrea Pirlo". And yet, that was precisely how teenage winger Andrea Pirlo was introduced to a British audience, when he replaced Roberto Baggio at Old Trafford in 1999.

He was neither "teenage" nor "winger" for long, turning 20 two months later and also changing position. First, he was converted into a deeplyingstrikerista, and then, when sent on loan to Brescia in 2001, a deeplyingplamakerista. Now, he's just Pirlo.

In the north-west of England, "Phil Chisnall" is the answer to a quiz question and in north London, "Sol Campbell" the start of a fight. But in Italy, the culture is different, top players passed around the top clubs like a cheap metaphor. Baggio, for example, represented Fiorentina, Juve, Milan and Inter; Christian Vieri was at Torino, Juve, Lazio, Inter and Milan; and Fabio Cannavaro moved through Napoli, Parma, Inter and Juve.

In any event, Pirlo leaving Inter for Milan was neither here nor there, because he was yet to establish himself, and in theory, his passage from Milan to Juve is nothing noteworthy either. In theory. In practice, it's little short of lunacy. He didn't leave for money, because of money, or because one team were better than other; Milan decided that they didn't need him. And seeing as his contract was up, he was available for free! Free! Pirlo, free!

But good players are often allowed to leave good teams, sometimes to facilitate improvement – Alex Ferguson, for example, sold Mark Hughes, Paul Ince and Ruud van Nistelrooy to excellent effect. Pirlo, though, is of different ilk, not simply one of the world's many brilliant footballers, but one of very few whom you want to watch until your eyes fall out. Gliding and swishing in languid, effortless, elegant arches, he sees things others can't, takes risks they couldn't, and generally just decides what happens, with amiable, classy sex appeal.

So, in 2010-11, Milan were Serie A champions, then packed him off to Juventus immediately afterwards. So, in 2011-12, Juventus were champions, Pirlo contributing more assists than any other player and voted Italian Footballer of the Year. So, Milan finished in second place, four points off the top. So, in 2012-13, Juventus won the league. So, Milan finished third, 15 points off the top. Free! Pirlo, Free! It's a mad, mad, mad, mad world. DH

5) Paul Lambert, Motherwell to Borussia Dortmund (1996)

The Bosman ruling changed many a player's life for the better, the currently incarcerated Jean-Marc Bosman being the exception that proves the rule. Steve McManaman is arguably the most successful British beneficiary of it, having left Liverpool for Real Madrid in the summer of 1999 to score a spectacular goal in the Champions League final a year later, before picking up a second winners' medal in 2002. But he was already established as a top-level act. Paul Lambert's Bosman bonanza was unquestionably more spectacular as a life-changer, because few had given him much in the way of consideration before he left North Lanarkshire for North Rhine-Westphalia in 1996.

In the summer of that year, nine Scottish-based players were snaffled up on frees under the new Bosman rules. Paul Kane and Gary Smith left Aberdeen for, respectively, Stavanger in Norway and Rennes in France, the latter also making off with Allan Johnston of Hearts. Ionikos of Greece signed Steven Tweed of Hibs and Craig Brewster of Dundee United, while Motherwell lost Rob McKinnon to FC Twente of the Netherlands and St Mirren bade farewell to Jamie Fullarton, who left for Bastia in France. The most high-profile move was made by John Collins, who went from Celtic to Monaco, though the highest eyebrows were raised by Borussia Dortmund, the new champions of Germany, who plundered Motherwell for 27-year-old Lambert, and immediately installed him in the engine room of a team containing Matthias Sammer, Jürgen Kohler, Andreas Möller, Karl-Heinz Riedle, Stefan Reuter, Stéphane Chapuisat and Paulo Sousa.

Few who had been paying any attention to the game in Scotland would have been archly arcing their brows, mind you. "It's an indication of the mistake a lot of English managers make when they think of Scottish football," suggested Lambert's agent, the former Partick Thistle and Leicester City striker Jim Melrose, at the time of the move. "They look no further than Rangers and Celtic and don't realise there are quite a number of good players outside of the Old Firm. I think some of the English managers have made a mistake, because they could have got Lambert at a reasonable fee. But it's Paul's good fortune that he's made it to Dortmund."

Damn straight it was. Lambert, who had been picking up an annual salary of around £25,000 during his first eight years as a pro at St Mirren and Motherwell, suddenly found himself trousering £300,000 a year, while living in a rent-free pile and wheelspinning around in a club Merc. Dortmund coach Ottmar Hitzfeld had been impressed with the player when his side met Motherwell in the Uefa Cup a couple of seasons earlier, and needed no second invitation to make off with one of the best unsung defensive midfielders in the business. His judgement – and that of Lambert and Melrose – was proven right the following May, when the player snuffed out Zinedine Zidane as Dortmund beat Juventus to become champions of Europe. SM

In 1985, football was rubbish. We know this because all those accorded a public platform insisted so, which proves it beyond the remotest doubt. Consequently, Roy Race, purveyor of all that is wholesomely sanctimonious, took it upon himself to "put the fun back in".

This was achieved, first of all, through the signing of notorious gag-machine, Bob Wilson. To an extent, this was reasonable – he's an indisputable mensch, and Charlie Carter was too old, Andy Styles too erratic. Wilson then helped Rovers set a record of 12 consecutive clean sheets, devising a system of signs with which to coach Styles from the touchline after a foot injury forced him out of the side.

Then, at Christmas time, Spandau Ballet played a concert at Mel Park, where they were joined on stage by a mystery man in a Santa outfit. Amazingly, it turned out to be none other than Roy Race, and, incredibly, he could sing. But it didn't end there, backstage lurking a convulsion of cryptic intrigue. "True," Racey told the band, "you lads could be worth your weight in Gold." About what could he possibly be talking?

That summer, Rovers toured the middle east state of Basran. Unfortunately, they walked directly into a coup, which began during their game against the national side. Though the team escaped the ground, the bus they commandeered was eventually involved in a crash and blown up by a car bomb, resulting in the deaths of eight players, while Racey missed the Mexico World Cup. Wilson, Hughes, Kemp and Norman had all stayed home, and were never mentioned again. DH